How to Play Politics Without Being a Total Loser
A Smart Generalist's Guide
Welcome to an insider-only edition! This is the ninth installment of Silicon Valley Startups, following:
The Basics (VC 101, Startups 101)
Finding a Career (How to Found a Silicon Valley Startup, How to Break Into Venture Capital, How to Join a Rocketship Startup, How to Choose)
Crushing Your Job (Getting Shit Done at Startup Speed, Company Building: My Playbook for Startup Ops)
This week, we’re talking about power and politics — meaning, how to play politics and get what you want, without being a total sleaze-bag.
I get it. Politics feel gross.
To you, “politics” might conjure up images of mob bosses and back-alley deals, or at least that horrific kid from college whose primary ambition was to become VP of Finance for the Student Government.
To me, “politics” reminds me of two stories — and they could not be more different from each other.
The first story is an example of politics at its worst.
I’m about 24 years old, I just finished by second year as a management consultant, and I have a problem.
My Year-End Rating, the single number that determines my bonus and raise, just came back and despite working my absolute hardest and rising to a notable position in the firm (that, honestly, is the equivalent of VP of Finance for Student Government), it’s less-than-stellar.
The reason why I got this rating is easy to diagnose: the ratings are determined by a bunch of senior folks sitting in one room together, but none of them have ever worked with me on a project. It’s an insane system. It doesn’t reward hard work — it rewards loyalty to the right Partners, who can then vouch for you when the Year-End process rolls around.
And so, for my third year, I decided to run an experiment. A little A/B test. I wouldn’t work as hard on my projects this year, and I’d instead plow all of my extra time and energy into (objectively less important) “extracurriculars” that are the Partners’ pet projects.
I’m ashamed to say that my plan worked to perfection. I got the top performance rating in my third year. I worked less overall, and did objectively worse work on my client-facing projects, but I played the political game much more adeptly, and I was rewarded for it.
I had figured out the “game” of consulting — and it made my skin squirm. This was the final nail in the consulting coffin; I resolved to find a career that was more meritocratic than political.
My second story about politics is more encouraging, and the reason for this post.
I’m now 27 years old, and a second-year MBA student at UC Berkeley. I’m desperately trying to find another career path that leads me away from consulting, and my hypothesis is that the answer lies in either venture capital or entrepreneurship.
I’ve decided to dip my toe into the VC waters by hosting of Berkeley’s annual “Venture Capital Speaker Series.” (As a public school, UC Berkeley relies on its students to do everything, includeing inviting fancy alumni back to campus.) I invited every VC that I knew — and far more that I didn’t know — to stop by campus and talk to us for an hour, and about ten of them accepted the invitation. One of those ten was Larsen Jensen.
Larsen gives us an incredible talk — he was an Olympic swimmer and a Navy SEAL before starting in VC — and before he leaves, I ask him if he can help me out on another random Berkeley VC thing I’m organizing. I honestly don’t remember what he says; he might have reluctantly agreed, or not. But in any case, I continue to bug him for the better part of the next year, trying to find some/any way to work with him. Nothing really takes. I feel like I am just asking this guy for stuff, rather than actually offering him anything useful, which — as a native Midwesterner — makes me feel physically ill because I’m being so transactional.
Fast forward two years. I’m now working at Astranis, and I realize that Larsen has a new job as well. He’s just started at Harpoon, a new VC firm focused on helping Silicon Valley startups break into the government market. Astranis hasn’t yet done any government work, but the US spends tens of billions of dollars making things for space every single year… it seems like a potentially perfect match. I ask my CEO, and he’s down to connect with Larsen. I ask Larsen, and he’s down to connect with my CEO.
I make the intro.
And then, about one year later, Harpoon has helped Astranis enter the government market — a significant line of business — and has earned a sizable allocation in Astranis’s Series C as a result.
Everyone was happy. Astranis got money and a great partner. Harpoon got an allocation in a fast-growing company. Larsen is happy when Harpoon is happy. Christian is happy that his relationship building (and, frankly, mooching) has finally resulted in something of value for Larsen.
Politics isn’t always gross
It would be nice to believe that opportunities in life can be earned just by putting your head down and working hard. That’s what I wanted when I left consulting. But that’s just not the way the world works — no man is an island.
You need to have people on your team. If you’re working as part of a team someone else leads, you also need people to give you opportunities to grow. But you can’t rely on people joining your team or giving you opportunities out of the goodness of their heart, that is, for no reason at all.
And that’s where politics come in: you need to convince others that by giving you what you want, they will get what they want.
🤝 The right way to approach politics
At its worst, politics is an interpersonal zero-sum game. At its best, politics is a way to help people who are happy to help you back.
The wrong way to play politics is to create zero value and try to capture more territory. Unfortunately, this is the path of least resistance. You see the power that your co-worker has acquired, and you try to take it for yourself. You see someone successful, and ask them for a favor (“can I pick your brain?”).
In some systems, there is no “right” way to play politics — and the dead giveaway that you’re living or working in such a system is when the rewards of that system are zero sum. In consulting, the performance evaluation system is explicitly zero-sum: it’s a force-ranked list, where only 10% of people can get the top rating. In Washington, D.C., there are only ever 548 electors in the electoral college, and your side needs to win more of them than the other guys.
So, here’s your first politics lesson: find positive sum games.
Startup investing is the ultimate game in which rising tides raise all ships. Larsen’s investment in Astranis has done remarkably well; he helped us enter the government market, he helped us by giving us cash, and we turned that cash into much more cash.
Other positive-sum games are everywhere, you just need to decode their rules to be able to play them, and win.
🔎 How to identify people who can help you
It’s easy to find the most powerful people in any given circle. In Silicon Valley, these folks are the founders of the fastest-growing companies (e.g., Patrick Collison), the leaders of the top VC firms (e.g., Marc Andreessen), and the people with large followings (e.g., Paul Graham).
The problem is that these people are insanely busy. They can help you, but realistically, they won’t. Why would they? It’s best not to target such people with your efforts, at least to begin.
Instead, look for people who are on the rise in professional communities you care about.
Look for people who are not yet founders, or VC leaders, or influencers, but might be in the near future. Look for the Director who is on the fast track to VP. Look for folks who have outsized influence for their [role, age, experience]. It’s much more likely that you can help a person on the rise than someone who has already reached the peak, which means you’re more likely to form a mutually beneficial relationship with them.
Early in your career, you’ll also want to look for diamonds in the rough. Lots of people reach out to founders right after they raise capital; relatively few people reach out to founders when their companies are being dragged in the media, or when they’ve recently shut down their companies.
And, finally, look for connectors who can introduce you to other people. You never want people to feel like they are just a connector, so don’t go too far down this path. But it certainly doesn’t hurt to be friends with well-connected people, particularly if they are well-connected in a different community/sub-community where your network is weaker, if only to get introduced into how those folks think and what they value.
💁🏻 How to make people want to help you
A good strategy for making people want to help you is to consistently show up, and be fun to work with.
Early in my Astranis career, I learned that the two co-founders would show up each Sunday to have an in-person meeting at our offices. And as fate would have it, after that, I just happened to have something to do in the office on a few Sundays. What a coincidence!
A better, more intentional strategy is to start a project that gives you plausible deniability to request someone’s advice/time.
Business school, for me, was a two-year sprint to build my Silicon Valley network as quickly as possible. I had trouble reaching out to people in the early days when my ask was “I’m a student who knows nothing, please help.” Some saints took my calls due to a mix of school pride and my persistence, but my hit rate was relatively low.
And then I started a startup — and things got considerably easier, because I had plausible deniability. I wasn’t reaching out just to “pick their brain,” I was reaching out because I needed real advice for real problems I was facing. And once I had a few wins under my belt (good pitches, customer progress, etc.), things were even easier because I had a reasonable path to becoming one of those fast-risers myself! (This is a magical feature of Silicon Valley: the fast-risers rise extremely fast, so people are generally much more giving of their time and energy than they would be in a static environment.)
The best strategy, however, is not to ask for anything at all: you should find ways to help people, even if there’s no obvious way that they can help you in the near term.
This is the real lesson from my story with Larsen: think of it from his perspective. Accepting the invitation to speak at Berkeley made sense because he had the chance to introduce himself to lots of potential fast-risers all at once. Humoring me, the most annoying of the bunch, made sense because I was working on a startup idea that had potential. And then those efforts paid off in a way that he couldn’t have predicted — I introduced him to the CEO of what would become one of the best investments in a fund he hadn’t even started yet.
If you find champions who are willing to humor you with their time — or, even better, who give you something to work on — you should do your best to over-deliver. Make them think that betting on you was the best decision they’ve ever made. Share your successes with them. Connect them to other people and opportunities that they might not see otherwise. Defend and amplify them in public.
And, remember, you should do this without expecting that they’ll ever be able to help you directly. It’ll be more effective, and you’ll feel less icky. There’s nothing wrong with helping people!
One final tip for the road: if you can be just slightly more shameless, it’ll be easier for others to keep you top of mind. This is a not-so-secret reason I love writing — I get to do something I love (improving my clarity of thought by getting it outside my brain), and I get a very positive side effect (reminding everyone who I am and what I care about). You don’t have to be a writer, but you should find a way to engage and re-engage your network on a periodic basis.
I hope that I’ve convinced you that politics doesn’t need to be gross.
If you’re terrible at politics, it likely will be gross: you’ll use people, you’ll discard them when they can no longer help you, and you’ll develop a reputation for being a “political” person.
But you don’t need to be terrible at politics. Find people who can help you, and then find ways to help them with no expectation of reciprocity. That’ll get you most of the way there.